HRP20160144T1 - Derivati etinila kao modulatori receptora metabotropskih glutamata - Google Patents
Derivati etinila kao modulatori receptora metabotropskih glutamata Download PDFInfo
- Publication number
- HRP20160144T1 HRP20160144T1 HRP20160144TT HRP20160144T HRP20160144T1 HR P20160144 T1 HRP20160144 T1 HR P20160144T1 HR P20160144T T HRP20160144T T HR P20160144TT HR P20160144 T HRP20160144 T HR P20160144T HR P20160144 T1 HRP20160144 T1 HR P20160144T1
- Authority
- HR
- Croatia
- Prior art keywords
- phenylethynyl
- pyridin
- image
- propionamide
- formula
- Prior art date
Links
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 title claims 5
- 102000016193 Metabotropic glutamate receptors Human genes 0.000 title 1
- 108010010914 Metabotropic glutamate receptors Proteins 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims 19
- 150000003839 salts Chemical class 0.000 claims 7
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 4
- 239000002253 acid Substances 0.000 claims 4
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 3
- 229910052739 hydrogen Inorganic materials 0.000 claims 3
- 239000001257 hydrogen Substances 0.000 claims 3
- 125000001424 substituent group Chemical group 0.000 claims 3
- 239000003814 drug Substances 0.000 claims 2
- 150000002431 hydrogen Chemical class 0.000 claims 2
- 239000000203 mixture Substances 0.000 claims 2
- 125000006555 (C3-C5) cycloalkyl group Chemical group 0.000 claims 1
- RNUOSMNJMUZUNS-UHFFFAOYSA-N 2,2-dimethyl-n-[5-(2-phenylethynyl)pyridin-2-yl]propanamide Chemical compound C1=NC(NC(=O)C(C)(C)C)=CC=C1C#CC1=CC=CC=C1 RNUOSMNJMUZUNS-UHFFFAOYSA-N 0.000 claims 1
- XZNIYOQXRDUMCY-UHFFFAOYSA-N 2,2-dimethyl-n-[5-(2-phenylethynyl)pyrimidin-2-yl]propanamide Chemical compound C1=NC(NC(=O)C(C)(C)C)=NC=C1C#CC1=CC=CC=C1 XZNIYOQXRDUMCY-UHFFFAOYSA-N 0.000 claims 1
- HWBFRCFPMYKQRP-UHFFFAOYSA-N 2,2-dimethyl-n-[6-(2-phenylethynyl)pyridazin-3-yl]propanamide Chemical compound N1=NC(NC(=O)C(C)(C)C)=CC=C1C#CC1=CC=CC=C1 HWBFRCFPMYKQRP-UHFFFAOYSA-N 0.000 claims 1
- CZUADVARASQGCU-UHFFFAOYSA-N 2-methoxy-2-methyl-n-[5-(2-phenylethynyl)pyridin-2-yl]propanamide Chemical compound C1=NC(NC(=O)C(C)(C)OC)=CC=C1C#CC1=CC=CC=C1 CZUADVARASQGCU-UHFFFAOYSA-N 0.000 claims 1
- LWJUFPGJSOBDQK-UHFFFAOYSA-N 2-methoxy-n-[5-(2-phenylethynyl)pyridin-2-yl]acetamide Chemical compound C1=NC(NC(=O)COC)=CC=C1C#CC1=CC=CC=C1 LWJUFPGJSOBDQK-UHFFFAOYSA-N 0.000 claims 1
- RHBYCEDHUUNXCL-UHFFFAOYSA-N 2-methyl-n-[5-(2-phenylethynyl)pyridin-2-yl]pentanamide Chemical compound C1=NC(NC(=O)C(C)CCC)=CC=C1C#CC1=CC=CC=C1 RHBYCEDHUUNXCL-UHFFFAOYSA-N 0.000 claims 1
- FKZRBSFGTIXFSO-UHFFFAOYSA-N 2-methylsulfanyl-n-[5-(2-phenylethynyl)pyridin-2-yl]acetamide Chemical compound C1=NC(NC(=O)CSC)=CC=C1C#CC1=CC=CC=C1 FKZRBSFGTIXFSO-UHFFFAOYSA-N 0.000 claims 1
- BJWFYNYCXPMRDO-UHFFFAOYSA-N 3-methyl-n-[5-(2-phenylethynyl)pyridin-2-yl]butanamide Chemical compound C1=NC(NC(=O)CC(C)C)=CC=C1C#CC1=CC=CC=C1 BJWFYNYCXPMRDO-UHFFFAOYSA-N 0.000 claims 1
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims 1
- 206010003805 Autism Diseases 0.000 claims 1
- 208000020706 Autistic disease Diseases 0.000 claims 1
- 208000001914 Fragile X syndrome Diseases 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 102000012777 Metabotropic Glutamate 5 Receptor Human genes 0.000 claims 1
- 108010065028 Metabotropic Glutamate 5 Receptor Proteins 0.000 claims 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 1
- 230000003281 allosteric effect Effects 0.000 claims 1
- 208000010877 cognitive disease Diseases 0.000 claims 1
- 230000006806 disease prevention Effects 0.000 claims 1
- 229940079593 drug Drugs 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical group 0.000 claims 1
- 125000001072 heteroaryl group Chemical group 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- MRNKGHIVWGFKKT-UHFFFAOYSA-N n,2,2-trimethyl-n-[5-(2-phenylethynyl)pyrimidin-2-yl]propanamide Chemical compound C1=NC(N(C(=O)C(C)(C)C)C)=NC=C1C#CC1=CC=CC=C1 MRNKGHIVWGFKKT-UHFFFAOYSA-N 0.000 claims 1
- ICIZAOBOELJTEG-UHFFFAOYSA-N n-[5-(2-phenylethynyl)pyridin-2-yl]butanamide Chemical compound C1=NC(NC(=O)CCC)=CC=C1C#CC1=CC=CC=C1 ICIZAOBOELJTEG-UHFFFAOYSA-N 0.000 claims 1
- IEEWOHAXHXPWHL-UHFFFAOYSA-N n-[5-(2-phenylethynyl)pyridin-2-yl]pentanamide Chemical compound C1=NC(NC(=O)CCCC)=CC=C1C#CC1=CC=CC=C1 IEEWOHAXHXPWHL-UHFFFAOYSA-N 0.000 claims 1
- WSNPFRDFJAYVKA-UHFFFAOYSA-N n-[5-[2-(1h-pyrrolo[2,3-b]pyridin-2-yl)ethynyl]pyridin-2-yl]acetamide Chemical compound C1=NC(NC(=O)C)=CC=C1C#CC1=CC2=CC=CN=C2N1 WSNPFRDFJAYVKA-UHFFFAOYSA-N 0.000 claims 1
- RCHUKVKOLIFTNH-UHFFFAOYSA-N n-[5-[2-(2,5-difluorophenyl)ethynyl]pyridin-2-yl]-2-methoxy-2-methylpropanamide Chemical compound C1=NC(NC(=O)C(C)(C)OC)=CC=C1C#CC1=CC(F)=CC=C1F RCHUKVKOLIFTNH-UHFFFAOYSA-N 0.000 claims 1
- WLTKTNOYOWUNAP-UHFFFAOYSA-N n-[5-[2-(3-fluorophenyl)ethynyl]pyridin-2-yl]-2,2-dimethylpropanamide Chemical compound C1=NC(NC(=O)C(C)(C)C)=CC=C1C#CC1=CC=CC(F)=C1 WLTKTNOYOWUNAP-UHFFFAOYSA-N 0.000 claims 1
- NYMXUGNIKMSYSK-UHFFFAOYSA-N n-[5-[2-(3-fluorophenyl)ethynyl]pyridin-2-yl]-2-methoxy-2-methylpropanamide Chemical compound C1=NC(NC(=O)C(C)(C)OC)=CC=C1C#CC1=CC=CC(F)=C1 NYMXUGNIKMSYSK-UHFFFAOYSA-N 0.000 claims 1
- 230000003287 optical effect Effects 0.000 claims 1
- 125000003566 oxetanyl group Chemical group 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 230000002265 prevention Effects 0.000 claims 1
- 201000000980 schizophrenia Diseases 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/72—Nitrogen atoms
- C07D213/75—Amino or imino radicals, acylated by carboxylic or carbonic acids, or by sulfur or nitrogen analogues thereof, e.g. carbamates
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/72—Nitrogen atoms
- C07D213/74—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D211/34—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/50—Pyridazines; Hydrogenated pyridazines
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
- C07D237/02—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings
- C07D237/06—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D237/10—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D237/20—Nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
- C07D237/02—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings
- C07D237/06—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D237/10—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D237/22—Nitrogen and oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/32—One oxygen, sulfur or nitrogen atom
- C07D239/42—One nitrogen atom
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Biomedical Technology (AREA)
- General Chemical & Material Sciences (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Epidemiology (AREA)
- Psychiatry (AREA)
- Hospice & Palliative Care (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyridine Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Liquid Crystal (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP11184257 | 2011-10-07 | ||
| PCT/EP2012/069605 WO2013050460A1 (en) | 2011-10-07 | 2012-10-04 | Ethynyl derivatives as metabotropic glutamate receptor modulators |
| EP12772100.9A EP2763969B1 (en) | 2011-10-07 | 2012-10-04 | Ethynyl derivatives as metabotropic glutamate receptor modulators |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20160144T1 true HRP20160144T1 (hr) | 2016-03-11 |
Family
ID=47016705
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HRP20160144TT HRP20160144T1 (hr) | 2011-10-07 | 2016-02-08 | Derivati etinila kao modulatori receptora metabotropskih glutamata |
Country Status (31)
| Country | Link |
|---|---|
| US (1) | US8530472B2 (ko) |
| EP (1) | EP2763969B1 (ko) |
| JP (1) | JP5840794B2 (ko) |
| KR (1) | KR101656966B1 (ko) |
| CN (1) | CN103857658B (ko) |
| AR (1) | AR088765A1 (ko) |
| BR (1) | BR112014008078A2 (ko) |
| CA (1) | CA2847096A1 (ko) |
| CL (1) | CL2014000818A1 (ko) |
| CO (1) | CO6900142A2 (ko) |
| CR (1) | CR20140093A (ko) |
| CY (1) | CY1117212T1 (ko) |
| DK (1) | DK2763969T3 (ko) |
| EA (1) | EA024993B1 (ko) |
| ES (1) | ES2556796T3 (ko) |
| HK (1) | HK1193596A1 (ko) |
| HR (1) | HRP20160144T1 (ko) |
| HU (1) | HUE026626T2 (ko) |
| IL (1) | IL231439A (ko) |
| IN (1) | IN2014CN02477A (ko) |
| MX (1) | MX354414B (ko) |
| PE (1) | PE20141555A1 (ko) |
| PL (1) | PL2763969T3 (ko) |
| PT (1) | PT2763969E (ko) |
| RS (1) | RS54511B1 (ko) |
| SG (1) | SG11201401307WA (ko) |
| SI (1) | SI2763969T1 (ko) |
| TW (1) | TWI458710B (ko) |
| UA (1) | UA110995C2 (ko) |
| WO (1) | WO2013050460A1 (ko) |
| ZA (1) | ZA201402068B (ko) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| UA113223C2 (xx) * | 2012-08-13 | 2016-12-26 | Арилетинілпіримідини | |
| CA2879489A1 (en) * | 2012-10-18 | 2014-04-24 | F.Hoffmann-La Roche Ag | Ethynyl derivatives as modulators of mglur5 receptor activity |
| AU2016273751B2 (en) | 2015-06-03 | 2020-04-02 | F. Hoffmann-La Roche Ag | Ethynyl derivatives |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2416442C (en) * | 2000-07-24 | 2010-06-08 | Krenitsky Pharmaceuticals, Inc. | Substituted 5-alkynyl pyrimidines having neurotrophic activity |
| GB0325956D0 (en) | 2003-11-06 | 2003-12-10 | Addex Pharmaceuticals Sa | Novel compounds |
| US7776869B2 (en) | 2004-10-18 | 2010-08-17 | Amgen Inc. | Heteroaryl-substituted alkyne compounds and method of use |
| WO2006048771A1 (en) | 2004-11-04 | 2006-05-11 | Addex Pharmaceuticals Sa | Novel tetrazole derivatives as positive allosteric modulators of metabotropic glutamate receptors |
| SI1863818T1 (sl) * | 2005-03-23 | 2010-05-31 | Hoffmann La Roche | Derivati acetilenil pirazolo pirimidina kot antagonisti mglur |
| GB0510139D0 (en) | 2005-05-18 | 2005-06-22 | Addex Pharmaceuticals Sa | Novel compounds B1 |
| US8853392B2 (en) | 2007-06-03 | 2014-10-07 | Vanderbilt University | Benzamide mGluR5 positive allosteric modulators and methods of making and using same |
| NZ581817A (en) | 2007-06-03 | 2012-05-25 | Univ Vanderbilt | Benzamide mglur5 positive allosteric modulators and methods of making and using same |
| HUE029837T2 (en) | 2008-07-29 | 2017-04-28 | Boehringer Ingelheim Int | 5-alkynyl pyrimidines |
| US8389536B2 (en) * | 2009-10-27 | 2013-03-05 | Hoffmann-La Roche Inc. | Positive allosteric modulators (PAM) |
-
2012
- 2012-04-10 UA UAA201404417A patent/UA110995C2/uk unknown
- 2012-09-27 US US13/628,128 patent/US8530472B2/en active Active
- 2012-10-04 SI SI201230401T patent/SI2763969T1/sl unknown
- 2012-10-04 MX MX2014003636A patent/MX354414B/es active IP Right Grant
- 2012-10-04 PE PE2014000497A patent/PE20141555A1/es active IP Right Grant
- 2012-10-04 KR KR1020147011407A patent/KR101656966B1/ko active IP Right Grant
- 2012-10-04 PT PT127721009T patent/PT2763969E/pt unknown
- 2012-10-04 CN CN201280049441.XA patent/CN103857658B/zh active Active
- 2012-10-04 ES ES12772100.9T patent/ES2556796T3/es active Active
- 2012-10-04 TW TW101136751A patent/TWI458710B/zh not_active IP Right Cessation
- 2012-10-04 SG SG11201401307WA patent/SG11201401307WA/en unknown
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